According to Hatfield et al, (Inorg. Chem. 1, 463 (1962)), tertiary alkyl amines have little tendency to coordinate with metal salts unless stabilized by chelation. However, complexes of trimethylamine and/or triethylamine have been reported with halides of various metals including lithium, beryllium, aluminum, gallium, germanium, tin, etc. It is also stated by Hatfield et al that triethylamine does not react with calcium or zinc halides at 25.degree. C. but gives stable 1 : 1 complexes with Co (II) halides.
Several transition metal complexes containing a monoquaternized tertiary diamine are known; Quagliano et al, J. Am. Chem. Soc., 92, 482 (1970), and X-ray diffraction data are reported for the diquaternized tertiary diamine complexes of ZnCl.sub.2 and ZnBr.sub.2 ; Brun et al C. R. Acad. Sci. Ser. C 279, 129 (1974).
Olah, Friedel-Crafts and Related Reactions, Interscience Publishers, New York, N. Y. (1963) Volume I, pages 734-736, page 735 refers to the system: aluminum chloride-hydrogen chloride-toluene. On page 735, reference is also made to "red oils", e.g. 6.28 toluene Al.sub.2 Br.sub.6 .multidot.HBr. Other "red oils" are referred to on pages 734 and 736. Some amine complexes are discussed by Olah one pages 571 and 583. See Volume II, Pages 425-427 for a discussion of in situ preparation of metal halides.
Since 1886, it has been known that toluene disproportionates in the presence of aluminum chloride to form benzene and xylenes; R. M. Roberts et al, Friedel-Crafts Alkylation Chemistry, Marcel Dekker, New York, N. Y. (1984), Pages 673-676.